Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide at 0℃; for 6h; | 90% |
With potassium tert-butylate; 18-crown-6 ether In diethyl ether for 1h; Ambient temperature; | 86% |
With potassium hydroxide In water at 20 - 37℃; | 85% |
1-methyl-1H-pyrazole-5-carboxylic acid
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
In neat (no solvent) at 235 - 250℃; | 81% |
Conditions | Yield |
---|---|
at 140℃; for 8h; atmospheric pressure; | 69% |
at 115 - 140℃; for 8 - 9h; | 14% |
Conditions | Yield |
---|---|
With sodium hydroxide | 60% |
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃; | 53% |
1-methyl-5-(trimethylsilyl)-1H-pyrazole
butyraldehyde
A
1-methyl-1H-pyrazole
B
5-(1-hydroxybutyl)-1-methylpyrazole
Conditions | Yield |
---|---|
cesium fluoride In N,N-dimethyl-formamide at 50℃; for 1.33333h; | A 30% B 10% |
Conditions | Yield |
---|---|
With sodium hydroxide; dimethyl sulfate |
4-bromo-1-methyl-1H-pyrazole
n-butyllithium
diethyl ether
A
1-methyl-1H-pyrazole
B
1-methyl-1H-pyrazole-4-carboxylic acid
Conditions | Yield |
---|---|
anschl. mit CO2 bei -70grad; |
Conditions | Yield |
---|---|
With ethanol; methylhydrazine sulfuric acid |
1,2-dimethyl-1H-pyrazol-2-ium iodide
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
bei der trocknen Destillation; |
bis(pyrazol-1-yl)methane
A
NH-pyrazole
B
1-methyl-1H-pyrazole
C
Tris(pyrazolyl)methane
Conditions | Yield |
---|---|
at 600 - 750℃; under 0.01 Torr; | A 25.2 % Chromat. B 10.0 % Chromat. C 30.8 % Chromat. |
at 600 - 750℃; under 0.01 Torr; | A 25.2 % Chromat. B 10 % Chromat. C 30.8 % Chromat. |
Conditions | Yield |
---|---|
With diethyl ether at 120℃; im Rohr; |
4-bromo-1-methyl-1H-pyrazole
diethyl ether
phenyllithium
A
1-methyl-1H-pyrazole
B
1-methyl-1H-pyrazole-4-carboxylic acid
C
bromobenzene
Conditions | Yield |
---|---|
anschl. mit CO2 bei -70grad; |
Conditions | Yield |
---|---|
With manganese(IV) oxide In dichloromethane at 0℃; | A 21 % Spectr. B 65 % Spectr. |
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
In benzene at 30℃; |
Conditions | Yield |
---|---|
With hydrogen sulfide |
methanol
malonaldehydebis(dimethylacetal)
A
NH-pyrazole
B
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: methanol With sulfuric acid; hydrazine hydrate at 0 - 25℃; Stage #2: malonaldehydebis(dimethylacetal) at 68 - 69℃; for 2h; Stage #3: With sodium hydroxide at 0 - 55℃; | A 82.2 %Chromat. B 16.4 %Chromat. |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 50 - 55℃; under 1551.49 - 2585.81 Torr; for 6h; | 16.4 %Chromat. |
Conditions | Yield |
---|---|
With carbonic acid dimethyl ester Reflux; |
Conditions | Yield |
---|---|
In methanol for 16h; Inert atmosphere; Reflux; |
4-iodo-1-methyl-1H-pyrazole
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; Pd/AlO(OH); water at 20℃; for 1.5h; Sonication; Schlenk technique; | > 95 %Chromat. |
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
In dimethyl sulfoxide |
1-methyl-1H-pyrazole
(1-methyl-1H-pyrazol-5-yl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: With Triisopropyl borate In tetrahydrofuran at -78 - 0℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran pH=6; | 100% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 0℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane pH=6; | 60% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at 5 - 20℃; for 1h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -70℃; for 0.5h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane at -15 - 20℃; for 1h; | 38% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With hydrogenchloride In water pH=6; |
Conditions | Yield |
---|---|
for 72h; | 100% |
1-methyl-1H-pyrazole
4-iodo-1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
With iodine; iodic acid In tetrachloromethane; water; acetic acid at 50℃; for 1.5h; | 99% |
With dihydrogen peroxide; iodine In water at 20℃; for 24h; | 91% |
Stage #1: 1-methyl-1H-pyrazole With iodine for 0.166667h; Large scale; Stage #2: With dihydrogen peroxide at 18 - 20℃; for 42.5h; Large scale; | 91% |
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
With CH2Cl2 In dichloromethane inert atmosphere; stirring (25°C, 2 h); solvent redn. (vac.), pptn. on hexane addn., filtn., washing (hexane), drying (vac.); elem. anal.; | 99% |
1-methyl-1H-pyrazole
rhodium (II) octanoate dimer
[Rh2(octanoato)4(1-methylpyrazole)]
Conditions | Yield |
---|---|
In chloroform (N2); a soln. of ligand added to Rh complex in CHCl3, stirred at room temp. for 1 h; evapd. (vac.); elem. anal.; | 99% |
1-methyl-1H-pyrazole
rhodium (II) octanoate dimer
[Rh2(octanoato)4(1-methylpyrazole)2]
Conditions | Yield |
---|---|
In chloroform (N2); a soln. of ligand added to Rh complex in CHCl3, stirred at room temp. for 1 h; evapd. (vac.); elem. anal.; | 99% |
1-methyl-1H-pyrazole
1-methyl-3-nitro-1H-pyrazole
Conditions | Yield |
---|---|
With silica-sulfuric acid impregnated with bismuth nitrate In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With bis(acetylacetonate)nickel(II); trimethylaluminum In hexane; toluene at 35℃; for 12h; | 96% |
1-methyl-1H-pyrazole
1-methyl-3,4-dinitropyrazole
Conditions | Yield |
---|---|
With bismuth(III) nitrate In tetrahydrofuran at 20℃; for 12h; | 96% |
With silica-sulfuric acid impregnated with bismuth nitrate In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Green chemistry; | 92% |
1-methyl-1H-pyrazole
cis-chloro(dicarbonyl)(1-methylpyrazole)rhodium(I)
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 6h; Inert atmosphere; | 96% |
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; Schlenk technique; | 96% |
1-methyl-1H-pyrazole
1-methyl-4-((phenylethynyl)sulfonyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In diethyl ether; hexane at 0℃; Stage #2: 1-methyl-4-((phenylethynyl)sulfonyl)benzene In diethyl ether for 0.25h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With chloro(dimethylsulfide) gold(I); silver(I) acetate; I,I-bis(acetoxy)iodobenzene In 1,4-dioxane at 100℃; for 15h; Inert atmosphere; regioselective reaction; | 96% |
1-methyl-1H-pyrazole
(4-bromo-6-formyl-benzothiazol-2-yl)-carbamic Acid tert-butyl Ester
{4-Bromo-6-[hydroxy-(2-methyl-2H-pyrazol-3-yl)-methyl]-benzothiazol-2-yl}-carbamic Acid tert-butyl Ester
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; methanol; hexane at -78 - 20℃; for 1.5h; Stage #2: (4-bromo-6-formyl-benzothiazol-2-yl)-carbamic Acid tert-butyl Ester In tetrahydrofuran; hexane at -58 - 20℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water | 95% |
Conditions | Yield |
---|---|
With 4,5-Diazafluoren-9-one; oxygen; palladium diacetate; trifluoroacetic acid; p-benzoquinone In 1,4-dioxane at 100℃; under 760.051 Torr; for 24h; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
In ethanol at 80℃; for 72h; | 94.3% |
1-methyl-1H-pyrazole
dimethyldimethoxysilan
Nonafluorobutanesulfonyl fluoride
B
dimethyldifluorosilane
Conditions | Yield |
---|---|
In diethyl ether 35°C , 24 h; | A 94% B n/a |
In diethyl ether 35°C , 24 h; | A 94% B n/a |
1-methyl-1H-pyrazole
cis-iodo(dicarbonyl)(1-methylpyrazole)rhodium(I)
Conditions | Yield |
---|---|
In dichloromethane at -10.16 - 20℃; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
In ethanol at 80℃; for 72h; | 93.2% |
1-methyl-1H-pyrazole
Triisopropyl borate
(1-methyl-1H-pyrazol-5-yl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: Triisopropyl borate In tetrahydrofuran at 20℃; | 93% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexanes at -78 - 0℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water for 1h; |
1-methyl-1H-pyrazole
4-fluorobenzaldehyde
(4-fluorophenyl)(1-methyl-1H-pyrazol-5-yl)methanol
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran at -78 - 20℃; for 1h; Stage #3: With ammonium chloride In water | 93% |
1-methyl-1H-pyrazole
Trimethyl borate
(1-methyl-1H-pyrazol-5-yl)boronic acid
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 4h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -70℃; | 93% |
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
With hydrogen bromide | 93% |
1-methyl-1H-pyrazole
5-iodo-1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With (PMDETA)2K2Mg(CH2SiMe3)4 at 0℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With iodine for 1h; Inert atmosphere; Schlenk technique; regioselective reaction; | 92% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.25h; Stage #2: With iodine In tetrahydrofuran at 20℃; for 1h; | 90% |
Stage #1: 1-methyl-1H-pyrazole With (THF)Li(TMP)Zn(tBu)2 In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; regioselective reaction; | 89% |
1-methyl-1H-pyrazole
1,3-bis[2,6-diisopropylphenyl]imidazolium chloride
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; Sealed tube; | 91% |
1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
With ferric(III) bromide; bromine In tert-butyl methyl ether at 0 - 20℃; | 90.5% |
With n-butyllithium; bromine In tetrahydrofuran at -76 - -70℃; Inert atmosphere; | 47.5% |
1-methyl-1H-pyrazole
5-Chloro-1-methylpyrazole
Conditions | Yield |
---|---|
With aluminum (III) chloride; chlorine In tert-butyl methyl ether at 0 - 20℃; | 90.5% |
1-methyl-1H-pyrazole
N,N-dimethyl-formamide
1-methyl-1H-pyrazole-5-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 2.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -20℃; for 1h; | 90% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 2.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -20℃; for 1h; | 90% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane for 1h; Inert atmosphere; | 58% |
1-methyl-1H-pyrazole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With C26H50CoN4O2 at 20℃; for 0.0833333h; Inert atmosphere; Glovebox; Stage #2: 1-methyl-1H-pyrazole at 80℃; for 48h; Inert atmosphere; Sealed tube; | 90% |
The 1-Methylpyrazole, with the CAS registry number 930-36-9, is also known as 1H-Pyrazole,1-methyl-. It belongs to the product categories of Pyrazoles & Triazoles; Building Blocks; Heterocyclic Building Blocks; Pyrazoles. This chemical's molecular formula is C4H6N2 and molecular weight is 82.10. What's more, its systematic name is 1-Methyl-1H-pyrazole. This chemical is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from strong oxidants.
Physical properties of 1-Methylpyrazole are: (1)ACD/LogP: -0.14; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.14; (4)ACD/LogD (pH 7.4): -0.14; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 19.97; (8)ACD/KOC (pH 7.4): 19.98; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 17.82 Å2; (13)Index of Refraction: 1.525; (14)Molar Refractivity: 25.25 cm3; (15)Molar Volume: 82.394 cm3; (16)Polarizability: 10.01×10-24cm3; (17)Surface Tension: 35.0 dyne/cm; (18)Density: 0.996 g/cm3; (19)Flash Point: 26.222 °C; (20)Enthalpy of Vaporization: 34.972 kJ/mol; (21)Boiling Point: 126.999 °C at 760 mmHg; (22)Vapour Pressure: 13.8 mmHg at 25°C.
Preparation: this chemical can be prepared by 1H-pyrazole and iodomethane at the ambient temperature. This reaction will need reagent potassium tert-butoxide and solvent diethyl ether with the reaction time of 1 hour. This reaction will also need catalyst 18-crown-6. The yield is about 86%.
Uses of 1-Methylpyrazole: it can be used to produce 1-methyl-4-nitro-1H-pyrazole. It will need reagents HNO3, H2SO4. The yield is about 60%.
When you are using this chemical, please be cautious about it as the following:
This chemical is flammable, so you should keep it away from sources of ignition - No smoking. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)SMILES: n1cccn1C
(2)Std. InChI: InChI=1S/C4H6N2/c1-6-4-2-3-5-6/h2-4H,1H3
(3)Std. InChIKey: UQFQONCQIQEYPJ-UHFFFAOYSA-N
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